Pyridine → Carbonic acid benzyl ester phenethyl ester

HRID 381223Notes

Reaction equation

HRID 381223 reaction equation
[CH2:1]([OH:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N1C=CC=CC=1.[CH2:16]([O:23][C:24](Cl)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl.CCOCC>[CH2:1]([O:9][C:24](=[O:25])[O:23][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 60542-PhenylethanolHCID 10387Benzyl chloroformate

Product 1

HCID 9859896Carbonic acid benzyl ester phenethyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 29.96 g phenethyl alcohol and 30 ml pyridine in 150 ml dichloromethane, 60.5 g benzylchloroformate was dropped in over 1 h 45 min while cooling in an ice-bath. After stirring over night at room temperature, the reaction was diluted with ether, washed with 2N HCl, NaHCO3, and water. After extraction with ether, the combined. organic layers were dried and evaporated to dryness. The residue was purified by silica gel chromatography to yield the product: 52.5 g of a colorless oil.

Workup

  1. additionwas dropped in over 1 h 45 min
  2. temperaturewhile cooling in an ice-bath
  3. washwashed with 2N HCl, NaHCO3, and water
  4. extractionAfter extraction with ether
  5. customorganic layers were dried
  6. customevaporated to dryness
  7. customThe residue was purified by silica gel chromatography
  8. customto yield the product

Sources & evidence

ORD record
ord-1e1eb61238154931890236e3f29b66d7
Source dataset
uspto-grants-2001_10
Patent number
US06306818B1

Reaction notes

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